Good Evening TJ and Welcome to ATP!
The trick to gardening in containers is to have large (10 - 15 gallon) containers that are well insulated. The containers should be double walled or externally insulated somehow. Hot roots are why potted plants fail.
I'm not sure where Asheville is so can't help you on the 'when'. Do you know what hardiness zone you are in? Do you know what state you are in?
Start cucumber seeds when all danger of frost is over - the weather has to be very warm before they will be happy outside.
Daisy